DE2203051C3 - Verfahren zur Herstellung von N-(2-Cyan-4-nitrophenyl)-N',N'-disubstituierten Formamidinen und N-(2-Cyan-6-nitrophenyl)-N',N'-disubstituierten Formamidinen - Google Patents
Verfahren zur Herstellung von N-(2-Cyan-4-nitrophenyl)-N',N'-disubstituierten Formamidinen und N-(2-Cyan-6-nitrophenyl)-N',N'-disubstituierten FormamidinenInfo
- Publication number
- DE2203051C3 DE2203051C3 DE2203051A DE2203051A DE2203051C3 DE 2203051 C3 DE2203051 C3 DE 2203051C3 DE 2203051 A DE2203051 A DE 2203051A DE 2203051 A DE2203051 A DE 2203051A DE 2203051 C3 DE2203051 C3 DE 2203051C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- cyano
- nitrophenyl
- disubstituted
- formamidines
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 2-cyano-4-nitrophenyl Chemical group 0.000 title claims description 12
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 13
- 229910017604 nitric acid Inorganic materials 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- QHFVILCBGHWQGA-UHFFFAOYSA-N N'-(2-cyano-4-nitrophenyl)methanimidamide Chemical compound C(#N)C1=C(C=CC(=C1)[N+](=O)[O-])NC=N QHFVILCBGHWQGA-UHFFFAOYSA-N 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VJQNMIUOXVVEKK-UHFFFAOYSA-N (4-bromo-2-cyanoanilino)methylidene-dimethylazanium hydrogen sulfate Chemical compound S(=O)(=O)(O)[O-].C(#N)C1=C(C=CC(=C1)Br)NC=[N+](C)C VJQNMIUOXVVEKK-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE794272D BE794272A (fr) | 1972-01-22 | Procede de preparation de n-(2-cyano-4-nitrophenyl) formamidines n',n'-disubstituees et de n-(2-cyano-6-nitrophenyl)formamidines n',n'-disubstituees | |
| DE2203051A DE2203051C3 (de) | 1972-01-22 | 1972-01-22 | Verfahren zur Herstellung von N-(2-Cyan-4-nitrophenyl)-N',N'-disubstituierten Formamidinen und N-(2-Cyan-6-nitrophenyl)-N',N'-disubstituierten Formamidinen |
| IT54939/72A IT974241B (it) | 1972-01-22 | 1972-12-21 | Procedimento per la produzione di formammidine n 2 ciano 4 nitrofenil n nbisostituite e formammidine n 2 ciano 6 nitrofenil n n bisosti tuite |
| CH72273A CH574917A5 (cg-RX-API-DMAC7.html) | 1972-01-22 | 1973-01-18 | |
| GB287173A GB1408843A (en) | 1972-01-22 | 1973-01-19 | Production of disubstituted formamidines |
| DD168332A DD101664A5 (cg-RX-API-DMAC7.html) | 1972-01-22 | 1973-01-19 | |
| JP48008729A JPS5749538B2 (cg-RX-API-DMAC7.html) | 1972-01-22 | 1973-01-22 | |
| US325737A US3862977A (en) | 1972-01-22 | 1973-01-22 | Nitration of N-(2-cyanophenyl)-N{40 ,N{40 -dialkylformamidines |
| FR7302120A FR2169119B1 (cg-RX-API-DMAC7.html) | 1972-01-22 | 1973-01-22 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2203051A DE2203051C3 (de) | 1972-01-22 | 1972-01-22 | Verfahren zur Herstellung von N-(2-Cyan-4-nitrophenyl)-N',N'-disubstituierten Formamidinen und N-(2-Cyan-6-nitrophenyl)-N',N'-disubstituierten Formamidinen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2203051A1 DE2203051A1 (de) | 1973-07-26 |
| DE2203051B2 DE2203051B2 (de) | 1980-07-31 |
| DE2203051C3 true DE2203051C3 (de) | 1981-04-30 |
Family
ID=5833752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2203051A Expired DE2203051C3 (de) | 1972-01-22 | 1972-01-22 | Verfahren zur Herstellung von N-(2-Cyan-4-nitrophenyl)-N',N'-disubstituierten Formamidinen und N-(2-Cyan-6-nitrophenyl)-N',N'-disubstituierten Formamidinen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3862977A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5749538B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE794272A (cg-RX-API-DMAC7.html) |
| CH (1) | CH574917A5 (cg-RX-API-DMAC7.html) |
| DD (1) | DD101664A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2203051C3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2169119B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1408843A (cg-RX-API-DMAC7.html) |
| IT (1) | IT974241B (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD926230S1 (en) | 2019-10-10 | 2021-07-27 | Ironhawk Industrial Distribution LLC | Curb guard |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2370558A (en) * | 1945-02-27 | Nitration of aromatic compounds | ||
| US2826611A (en) * | 1956-02-02 | 1958-03-11 | Dow Chemical Co | Process for making ar-dinitro-phenylureas |
| US3711552A (en) * | 1970-03-16 | 1973-01-16 | Sherwin Williams Co | Process for the manufacture of n,n-bis-(2-chloroethyl)-2-nitro-4-alkylaniline |
| DE2115625B2 (de) * | 1971-03-31 | 1978-07-06 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von N-o-Cyanophenyl-N', N'-disubstituierten Formamidinen und deren Salzen |
-
0
- BE BE794272D patent/BE794272A/xx unknown
-
1972
- 1972-01-22 DE DE2203051A patent/DE2203051C3/de not_active Expired
- 1972-12-21 IT IT54939/72A patent/IT974241B/it active
-
1973
- 1973-01-18 CH CH72273A patent/CH574917A5/xx not_active IP Right Cessation
- 1973-01-19 GB GB287173A patent/GB1408843A/en not_active Expired
- 1973-01-19 DD DD168332A patent/DD101664A5/xx unknown
- 1973-01-22 FR FR7302120A patent/FR2169119B1/fr not_active Expired
- 1973-01-22 US US325737A patent/US3862977A/en not_active Expired - Lifetime
- 1973-01-22 JP JP48008729A patent/JPS5749538B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2169119A1 (cg-RX-API-DMAC7.html) | 1973-09-07 |
| US3862977A (en) | 1975-01-28 |
| DE2203051B2 (de) | 1980-07-31 |
| GB1408843A (en) | 1975-10-08 |
| BE794272A (fr) | 1973-07-19 |
| JPS5749538B2 (cg-RX-API-DMAC7.html) | 1982-10-22 |
| IT974241B (it) | 1974-06-20 |
| FR2169119B1 (cg-RX-API-DMAC7.html) | 1976-05-14 |
| JPS4881831A (cg-RX-API-DMAC7.html) | 1973-11-01 |
| CH574917A5 (cg-RX-API-DMAC7.html) | 1976-04-30 |
| DE2203051A1 (de) | 1973-07-26 |
| DD101664A5 (cg-RX-API-DMAC7.html) | 1973-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) |